Diethyl[2-(4-nitrophenoxy)ethyl]amine → 4-(2-(Diethylamino)ethoxy)aniline

HRID 639375Notes

Reaction equation

HRID 639375 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:16]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:17]

Participants

4

Reactant 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amine

Product 1

HCID 4189324-(2-(Diethylamino)ethoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10 g (42 mMol) of Diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine is dissolved in 100 mL of ethanol and subjected to catalytic hydration at rt using 894 mg of Pd/C. After filtration trough HYFLO and removal of the solvent under reduced pressure, the crude product is purified by bulb-to-bulb distillation (140° C.) to obtain 4-(2-diethylamino-ethoxy)-phenylamine. Title compound: ES-MS: 209 [M+H]+; single peak at tR=2.3 min (System 2).

Workup

  1. customsubjected to catalytic hydration at rt
  2. filtrationAfter filtration trough HYFLO and removal of the solvent under reduced pressure
  3. distillationthe crude product is purified by bulb-to-bulb distillation (140° C.)

Sources & evidence

ORD record
ord-915d084862c245b1b1434375794e11ad
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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